Fluorobenzene → (4-Fluorophenyl)(pyridin-3-yl)methanone

HRID 2393639Notes

Reaction equation

HRID 2393639 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[O:9])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 10008FluorobenzeneHCID 14798Sodium HydroxideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 6451240Aluminum(III) Chloride

Product 1

HCID 762660(4-Fluorophenyl)(pyridin-3-yl)methanone

Conditions

Temperature
0 °C

Procedure

To a suspension of 140 g of nicotinic acid chloride hydrochloride in 500 ml of fluorobenzene cooled to 0° C. are added 280 g of aluminum chloride portionwise. The mixture is held under reflux for 6 hours, cooled and then poured onto ice. After the addition of sodium hydroxide up to pH=8, the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulfate and then evaporated under vacuum. The residue crystallizes in a pentane/diisopropyl ether mixture giving 108.5 g of 3-(4-fluorobenzoyl)pyridine in the form of crystals melting at 91° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionthe mixture is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue crystallizes in a pentane/diisopropyl ether mixture

Sources & evidence

ORD record
ord-c83db7fed98949f39a4f6dce33a2dfb6
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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